CURRICULUM VITAE DR. JUSTIN S. MILLER Associate Professor 3324 Dandelion Trail Department of Chemistry Canandaigua, NY 14424 Hobart and William Smith Colleges Phone: (315) 781-3884 Geneva, NY 14456 Email: [email protected] Web: http://campus.hws.edu/academic/popup.asp?id=366 EDUCATION Sloan-Kettering Institute for Cancer Research Postdoctoral Fellow (2001 – 2004), Advisor: Dr. Samuel J. Danishefsky Massachusetts Institute of Technology Ph.D., Organic Chemistry (2001), Advisors: Dr. Daniel S. Kemp, Dr. Scott C. Virgil • Dissertation: “I. Efforts towards the Synthesis of CP-263,114. II. On Solubilized, Spaced Polyalanines and Amino Acid -Helix Propensities.” • Graduate Student Teaching Award (1998) Princeton University A.B., Chemistry (1995), Advisor: Dr. Jeffrey Schwartz • Senior thesis: “The Reduction of Methyl Cinnamate by Titanocene Borohydride: A Mechanistic Study.” ACADEMIC APPOINTMENTS Associate Professor, organic chemistry, Hobart and William Smith Colleges (HWS) (2010 – present; Chair 2013 – present) Assistant Professor, organic chemistry, Hobart and William Smith Colleges (HWS) (2004 – 2010) Research interests • Peptide and protein synthetic methodology • Organic synthesis of bioactive molecules • Principles of bioorganic chemistry Courses taught • Introductory and intermediate organic chemistry, including laboratory • Bonding with Food: The Chemistry of Food Preparation, Production, and Policy • Advanced organic chemistry • Introductory general chemistry, including laboratory EXTERNAL GRANT FUNDING co-PI, NSF – Transforming Undergraduate Education in STEM (NSF-TUES) (2011 – 2014) • ($180,000) “NSF-TUES: Transforming Cell Biology and Organic Chemistry through Incorporation of the HDACi Cancer Therapeutic Laboratory Project” PI, National Institutes of Health Academic Research Enhancement Award (NIH-AREA) (2010 – 2014) • ($355,523) “NIH-AREA: Synthesis of Anticancer HDAC Inhibitor Natural Products and Analogs” PI, National Science Foundation Major Research Instrumentation (NSF-MRI) Award (2007 – 2010) • ($342,000) “MRI: Acquisition of an NMR Spectrometer to Advance Active Undergraduate Education and Research Programs” Research Corporation Cottrell College Science Award (2005 – 2009) • ($40,218 + $15,000 institutional matching) “Solid-Phase Synthesis of Cyclic, Cysteine- Containing Natural Products and Analogues” Camille and Henry Dreyfus Start-up Award (2004 – 2009) • ($30,000) “Solid-Phase Synthesis of Peptide Bioconjugates and Peptidic Natural Products” U.S. Army Prostate Cancer Research Postdoctoral Training Award (2003 – 2004) • ($98,000) “Toward a Diagnostic Immunoassay Specific for Prostate Cancer: Chemical Synthesis of Homogeneous N-Linked Prostate Specific Antigen Glycopeptides” Page 1 of 7 CURRICULUM VITAE DR. JUSTIN S. MILLER

PUBLICATIONS (undergraduate coauthors in bold) (13) N. A. Calandra, Y. L. Cheng, K. A. Kocak, and J. S. Miller. “Total Synthesis of Spiruchostatin A via Chemoselective Macrocyclization using an Accessible Enantiomerically Pure Latent Thioester.” Org. Lett. 2009, 11(9), 1971-1974.

(12) R. J. Moreau, C. R. Schubert, K. A. Nasr, M. Török, J. S. Miller, R. J. Kennedy, and D. S. Kemp. “Context-Independent, Temperature-Dependent Helical Propensities for Amino Acid Residues.” J. Am. Chem. Soc. 2009, 131(36), 13107-13116.

(11) V. Y. Dudkin, J. S. Miller, A. S. Dudkina, C. Antczak, D. A. Scheinberg, and S. J. Danishefsky. “Toward a Prostate Specific Antigen-Based Prostate Cancer Diagnostic Assay: Preparation of Keyhole Limpet Hemocyanin-Conjugated Normal and Transformed Prostate Specific Antigen Fragments.” J. Am. Chem. Soc. 2008, 130(41), 13598-13607.

(10) G. E. Job, R. J. Kennedy, Heitmann, B., J. S. Miller, S. M. Walker, and D. S. Kemp. “Temperature- and Length-Dependent Energetics of Formation for Polyalanine Helices in Water: Assignment of wAla(n,T) and Temperature-Dependent CD Ellipticity Standards.” J. Am. Chem. Soc. 2006, 128(25), 8227-8233. (9) J. D. Warren, J. S. Miller, S. J. Keding, and S. J. Danishefsky. “Toward Fully Synthetic Glycoproteins by Ultimately Convergent Routes: A Solution to a Long-Standing Problem.” J. Am. Chem. Soc. 2004, 126, 6576-6578. (8) V. Y. Dudkin, J. S. Miller, and S. J. Danishefsky. “Chemical Synthesis of Normal and Transformed PSA Glycopeptides.” J. Am. Chem. Soc. 2004, 126, 736-738.

(7) J. S. Miller, V. Y. Dudkin, G. J. Lyon, T. W. Muir, and S. J. Danishefsky. “Toward Fully Synthetic N-Linked Glycoproteins.” Angew. Chem. Int. Ed. 2003, 42(4), 431-434.

(6) V. Y. Dudkin, J. S. Miller, and S. J. Danishefsky. “A Concise Route to the Core Pentasaccharide of N-Linked Glycoproteins.” Tetrahedron Lett. 2003, 44(9), 1791-1793. (5) P. Wallimann, R. J. Kennedy, J. S. Miller, W. Shalongo, and D. S. Kemp. “Dual Wavelength Parametric Test of Two-State Models for Circular Dichroism Spectra of Helical Polypeptides: Anomalous Dichroic Properties of Alanine-Rich Peptides.” J. Am. Chem. Soc. 2003, 125(5), 1203- 1220.

(4) J. S. Miller, R. J. Kennedy, and D. S. Kemp. “Solubilized, Spaced Polyalanines: A Context-Free System for Determining Amino Acid -Helix Propensities.” J. Am. Chem. Soc. 2002, 124(6), 945- 962.

(3) W. Maison, R. J. Kennedy, J. S. Miller, and D. S. Kemp. “C-Terminal Helix Capping Propensities in a Polyalanine Context for Amino Acids Bearing Nonpolar Aliphatic Side Chains.” Tetrahedron Lett. 2001, 42(30), 4975-4977.

(2) J. S. Miller, R. J. Kennedy, and D. S. Kemp. “Short, Solubilized Polyalanines Are Conformational Chameleons: Exceptionally Helical If N- and C-Capped with Helix Stabilizers, Weakly to Moderately Helical If Capped with Rigid Spacers.” Biochemistry, 2001, 40(2), 305-309.

(1) J. M. Schmitt, G. X. Zhou, and J. Miller. “Measurement of blood hematocrit by dual-wavelength near-IR photoplethysmography.” Proc. SPIE-Int. Soc. Opt. Eng. 1992, 1641 (Physiol. Monit. Early Detect. Diagn. Methods), 150-61.

Page 2 of 7 CURRICULUM VITAE DR. JUSTIN S. MILLER PATENTS (2) S. J. Danishefsky, V. Y. Dudkin, J. S. Miller, D. A. Scheinberg, and C. Antczak. “Preparation of normal and transformed PSA glycopeptide conjugates for diagnostic and therapeutic applications.” U.S. Pat. Appl. Publ. 2006, 124 pp. Patent application cont.-in-part of Appl. No. PCT/03US/38453. (1) S. J. Danishefsky, V. Y. Dudkin, and J. S. Miller. “Preparation of Prostate Specific Antigens and Conjugates of Diagnosis and Treatment of Cancer.” PCT Int. Appl. 2004, 257 pp. Patent application: WO 2003-US38453.

PRESENTATIONS (undergraduate coauthors in bold) (22) G. B. Shelkey, W. S. Perkins, X. Zang, L. Peraro, S. L. Cramer, J. N. Garofalo, T. R. Blum, and J. S. Miller. “Cyclic, cysteine-containing depsipeptide synthesis via latent thioester key intermediates.” 43rd ACS National Organic Chemistry Symposium, Seattle, WA, Jun 23-27, 2013. (21) W. J. Bowyer, J. S. Miller, and C. Forbes. “Kitchen as laboratory: Two courses at two very different levels.” Abstracts of Papers, 245th ACS National Meeting, New Orleans, LA, Apr 7-11, 2013, CHED-1704. (oral) (20) L. Peraro and J. S. Miller. “Incorporating original research into the organic teaching laboratory: The HDACi Cancer Therapeutic Laboratory Project.” Abstracts of Papers, 245th ACS National Meeting, New Orleans, LA, Apr 7-11, 2013, CHED-1614. (oral) (19) J. S. Miller and G. L. Sacks. “Chemistry of Cajun Cooking Competition.” Abstracts of Papers, 245th ACS National Meeting, New Orleans, LA, Apr 7-11, 2013, CHED-83.

(18) X. Zang, L. Peraro, H. K. Shah, G. B. Shelkey, M. A. Mahajan, and J. S. Miller. “Solid-phase synthesis of depsipeptidic potential anticancer compounds using latent thioesters.” Abstracts of Papers, 245th ACS National Meeting, New Orleans, LA, Apr 7-11, 2013, ORGN-204.

(17) W. S. Perkins, X. Zang, L. Peraro, H. K. Shah, N. M. Zanghi, and J. S. Miller. “Solid-Phase Synthesis of Depsipeptidic Anticancer Natural Products and Analogs via Improved Latent Thioester Mediated Solid-Phase Methodology.” Abstracts of Papers, 243rd ACS National Meeting, San Diego, CA, Mar 25-29, 2012, ORGN-610. (16) D. M. Wholly, W. S. Perkins, H. K. Shah, and J. S. Miller. “Solid-Phase Synthesis of Depsipeptidic Anticancer Natural Products and Analogs.” Abstracts of Papers, 241st ACS National Meeting, Anaheim, CA, Mar 27-31, 2011, ORGN-163. (15) T. R. Blum, H. K. Shah, X. Zang, W. S. Perkins, A. R. Korn, D. M. Wholly, and J. S. Miller. “Solution- and Solid-Phase Synthesis of Potential Anticancer HDAC Inhibitors.” Abstracts of Papers, 240th ACS National Meeting, Boston, MA, Aug 22-26, 2010, ORGN-937. (14) J. S. Miller. “Responsive Lecturing: Keeping the Tradition and Improving the Pedagogy.” HWS New Faculty Orientation, Aug 25, 2009. (invited lecture)

(13) D. M. Wholly, T. R. Blum, J. A. Walkley, K. A. Hlavac, and J. S. Miller. “Total Synthesis of Cysteine-Containing, Depsipeptidic Natural Products in Solution and on the Solid Phase via Chemoselective Macrocyclization Using Latent Thioester Solid-Phase Linkers.” Abstracts of Papers, 238th ACS National Meeting, Washington, D.C., Aug 16-20, 2009, ORGN-785. (12) J. S. Miller. “Fighting Cancer One Molecule at a Time? A Total Synthesis of Spiruchostatin A.” Illinois Wesleyan University Natural Science Colloquium Series, Apr 3, 2009. (invited lecture)

(11) J. S. Miller. “Lecturing Techniques that Engage Students.” HWS Faculty Institute: Teaching Practices in Context, Jan 15, 2009. (invited lecture)

Page 3 of 7 CURRICULUM VITAE DR. JUSTIN S. MILLER (10) J. S. Miller. “Fighting Cancer One Molecule at a Time? A Total Synthesis of Spiruchostatin A.” Ithaca College Chemistry Department Seminar, Dec 9, 2008. (invited lecture)

(9) K. A. Perri, N. A. Calandra, D. M. Wholly, and J. S. Miller. “Key intermediate en route to the cyclic, cysteine-containing natural products Spiruchostatin A and B using a thioester equivalent ester functionality.” Abstracts of Papers, 236th ACS National Meeting, Philadelphia, PA, Aug 17-21, 2008, ORGN-467. (8) J. S. Miller. “What is an NMR, and why should anyone care that we got one?” Faculty Lunch Seminar Series, October, 2007. (Lecture)

(7) N. D. Valente, K. A. Kocak, Y.-L. Cheng, and J. S. Miller. “Toward the Fmoc Solid-Phase Synthesis of Native Chemical Ligation Precursors using Thioester Equivalent Ester Linkers.” Abstracts of Papers, 234th ACS National Meeting, Boston, MA, Aug 19-23, 2007, ORGN-904.

(6) K. A. Kocak, K. A. Perri, Y.-L. Cheng, and J. S. Miller. “Efficient Synthetic Route Toward the Cyclic, Cysteine-Containing Natural Products FK228 and the Spiruchostatins.” Abstracts of Papers, 234th ACS National Meeting, Boston, MA, Aug 19-23, 2007, ORGN-840.

(5) K. S. McMenaman, Y.-L. Cheng, S. M. Weinstein, and J. S. Miller. “Thioester Equivalent Linkers for the Fmoc Solid-Phase Synthesis of Native Chemical Ligation Precursors.” Abstracts of Papers, 35th Northeast Regional Meeting of the American Chemical Society, Binghamton, NY, Oct 5-7, 2006, NRM-447. (4) Y.-L. Cheng, G. M. Lippa, Z. J. Schonfield, K. A. Kocak, and J. S. Miller. “Toward the Solid- Phase Synthesis of Cyclic, Cysteine-Containing, Depsipeptidic Natural Products FK228 and the Spiruchostatins.” Abstracts, 35th Northeast Regional Meeting of the American Chemical Society, Binghamton, NY, Oct 5-7, 2006, NRM-445.

(3) J. D. Warren, J. S. Miller, and S. J. Danishefsky. “Convergent Synthesis of Bifunctional Glycopeptides Bearing Differential Glycans.” Abstracts of Papers, 228th ACS National Meeting, Philadelphia, PA, Aug. 22-26, 2004, ORGN-301.

(2) J. S. Miller. “(Glyco)Peptides: Synthesis, Structure, and Application.” Columbia University Chemistry Department Seminar, May, 2003. (Lecture) (1) J. S. Miller. “Efforts Towards the Synthesis of CP-263,114, A Highly Oxygenated Natural Product.” Organic Chemistry Graduate Symposium, May, 1999. (Lecture)

RESEARCH EXPERIENCE Professor, organic chemistry, HWS (Assistant, 2004 – 2010; Associate, 2010 – present) • Design and construction of linkers for solid-phase peptide synthesis • Synthesis of cysteine-containing natural products and analogues Postdoctoral Research in bioorganic chemistry, SKI (2001 – 2004) • Design of synthetic methodology for N-linked glycoprotein conjugates • Synthesis of prostate specific antigen (PSA) glycopeptides • Complex oligosaccharide synthesis Graduate Research in organic and bioorganic chemistry, MIT (1995 – 2001) • Design of a construct for studying the secondary structure of insoluble peptides • Synthesis and characterization of solubilized polyalanines • Determination of amino acid -helical propensities • Total synthesis of naturally occurring fungal metabolites Senior Thesis Research in organometallic chemistry, Princeton (1994 – 1995) • Mechanistic study of carbonyl reduction via metallocene borohydride reagents

Page 4 of 7 CURRICULUM VITAE DR. JUSTIN S. MILLER Undergraduate Research in inorganic chemistry, Princeton (1994) • Preliminary design and synthesis of potential chemotherapy drugs Summer Intern at the National Institutes of Health (1991 – 1993) • Techniques for diagnosis of cancer and Gaucher’s disease • Nuclear magnetic resonance (NMR) imaging techniques • NMR circuitry design and construction • Development of a practical medical device for measuring blood hemoglobin content SERVICE AND ADMINISTRATIVE EXPERIENCE HWS Center for Teaching and Learning (CTL) Teaching Fellows program (2007 – present) • Chemistry department liaison • Helped initiate the program HWS Honors program (2005 – present) • Honors advisor, Wade Perkins (2012) • Honors advisor, Deirdre Wholly (2011) • Honors advisor, Travis Blum (2010) • Honors advisor, Kimberly Hlavac (2009) • Honors advisor, Yim Ling Cheng (2007) • Honors Faculty Examiner (Emily Perkins, Lindsey Haun) • Honors Field Examiner (Mike Liquori, Deirdra Evers, Megan Rechin, Catherine Downey) Instrument care, maintenance responsibilities (HWS) • Departmental SolvTek dry solvent purification system (2005 – present) • Varian MR 400 MHz spectrometer (2008 – 2011) Instrument care, maintenance responsibilities (Danishefsky Group Laboratory Manager, 2002 – 2004) • Waters ZQ (and ZMD) with Micromass LCMS system • PE Biosystems automated peptide synthesizer • Labconco FreeZone 2.5 L lyophilizer • Waters analytical and semiprep HPLC systems HWS Committee on Standards (2009 – 2011; Chair 2010 – 2011) HWS Health Professions Advisory Committee (2006 – present; Chair 2011 – present) Health Professions Steering Committee (Chair, initiated in 2012 – present) Barry M. Goldwater Scholarship Committee (2008 – 2011) Elizabeth Blackwell Scholarship Committee (2008 – present) NSF reviewer (2007 – present) Reviewer: Organic Letters, Tetrahedron Letters, Mini Reviews in Organic Chemistry, Norton Publishing Group, Wiley International, Fundação para a Ciência e a Tecnologia (FCT, Portuguese Foundation for Science) (2008 – present) HWS Club advising • Ultimate Disc Club advisor (2010 – present) • Chem Club advisor (2004 – 2007) • Glassblowing Club advisor (2005 – 2006), assisted in forming the club Laboratory Safety • New York City Fire Department Charge of Chemical Laboratory Fitness (2002 – 2004) • MIT Chemistry Department Safety Committee (1999 – 2000) • MIT Laboratory Group Safety Coordinator (1998 – 2001) PROFESSIONAL MEMBERSHIPS American Chemical Society (ORGN: 1996 – present; AGFD: 2012 – present) Sigma Xi Scientific Research Society (2005 – 2009) Page 5 of 7 CURRICULUM VITAE DR. JUSTIN S. MILLER UNDERGRADUATE RESEARCH STUDENTS (28) Alysa B. Sadkin, William Smith ’15 (beginning Fall, 2013) (27) Amanda C. Rimsa, William Smith ’15 (beginning Fall, 2013) (26) Janae N. Garofalo, William Smith ’15 (May 2013 – present), “Toward a Solid-Phase Synthesis of HDAC Inhibitor Spiruchostatin A” (25) Stephanie L. Cramer, William Smith ’15 (May 2013 – present), “HDACi Cancer Therapeutic Laboratory Project: Depsipeptide Analog Synthesis” (24) Melissa A. Mahajan, William Smith ’15 (May 2012 – December 2012), “Toward an Optimized Synthesis of HDAC Inhibitor Spiruchostatin A” (23) Gregory B. Shelkey, Hobart ’14 (Sep 2011 – present), “New Reaction Conditions for Latent Thioester Chemoselective Ligation” (22) Nicole M. Zanghi, William Smith ’14 (May 2011 – May 2012), “Solid-Phase Synthesis of Anticancer Agent FK228” (21) Leila Peraro, William Smith ’13 (May 2011 – May 2013), “HDACi Cancer Therapeutic Laboratory Project: Depsipeptide Analog Synthesis” (20) Heli K. Shah, William Smith ’13 (May 2010 – May 2013), “Attempted Synthesis of ” (19) Xiaoyu Zang, William Smith ’13 (May 2010 – present), “Total Synthesis of Anticancer HDAC Inhibitor Natural Products and Analogs” (18) Ariella R. Korn, William Smith ’12 (May 2010 – Aug 2010), “Synthesis of an Enantiomerically Pure Linker for Chemoselective Ligation” (17) Wade S. Perkins, Hobart ’12 (May 2010 – May 2012), “Preparation of a Nagao-Functionalized Hydroxymercaptoheptanoate for Cyclic Depsipeptide Analog Synthesis” (2010) and “New Reaction Conditions for Unmasking Latent Thioesters” (2011) (16) Travis R. Blum, Hobart ’10 (May 2009 – May 2010), “Synthesis of Cysteine-Containing, Depsipeptidic Natural Products and Analogs in Solution and on the Solid Phase via Chemoselective Macrocyclization using Latent Thioesters” (15) Janelle A. Walkley, William Smith ’09 (May 2009 – Aug 2009), “Total Synthesis of Cysteine- Containing, Depsipeptidic Natural Products on the Solid Phase using Latent Thioester Linkers” (14) Kimberly A. Hlavac, William Smith ’09 (Sep 2008 – May 2009), “Crucial Intermediates for the Solid-Phase Synthesis of FK228 and the Spiruchostatins” (13) Yessica Baez-Sosa, William Smith ’09 (May 2008 – Jan 2009), “Crucial Intermediates for the Solid- Phase Synthesis of FK228 and the Spiruchostatins” (12) Deirdre M. Wholly, William Smith ’11 (May 2008 – May 2011), “Linkers for the Solid-Phase Synthesis of Latent Peptide Thioesters” and “Toward the Total Synthesis of Anticancer Agent FK228” (11) Nicole A. Calandra, William Smith ’09 (May 2008 – May 2009), “The Total Synthesis of Potential Anticancer Agent Spiruchostatin A” (10) Katherine A. Perri, William Smith ’10 (May 2007 – Aug 2008), “Toward the Total Synthesis of Cyclic, Cysteine-Containing Natural Products FK228 and the Spiruchostatins”

Page 6 of 7 CURRICULUM VITAE DR. JUSTIN S. MILLER (9) Nicholas D. Valente, Hobart ’09 (May 2007 – Aug 2007), “Linkers for the Solid-Phase Synthesis of Cyclic, Cysteine-Containing Natural Products FK228 and the Spiruchostatins” (8) Kimberly A. Kocak, William Smith ’08 (Jun 2005 – May 2008), “Toward the Solid-Phase Synthesis of Cyclic, Cysteine-Containing Natural Products FK228 and the Spiruchostatins” (7) Zachary J. Schonfield, Hobart ’08 (Jun 2005 – Aug 2006), “Crucial Intermediates for the Solid-Phase Synthesis of FK228 and the Spiruchostatins” (6) Yim Ling Cheng, William Smith ’07 (Jun 2005 – May 2007), “Toward the Total Synthesis of Potential Anticancer Agent Spiruchostatin A and Its Analogs” (5) Kathryn S. McMenaman, William Smith ’07 (Sep 2005 – Jan 2006), “Completion of Two Resins for the Solid-Phase Synthesis of Potential Anticancer Agents FK228 and the Spiruchostatins” (4) Geoffrey M. Lippa, Hobart ’07 (Jun 2005 – Jul 2006), “An Intermediate for the Solid-Phase Synthesis of Potential Anticancer Agents FK228 and Spiruchostatins A and B” (3) Sarah M. Weinstein, William Smith ’07 (Jun 2005 – Jul 2005), “Potential Linkers for the Solid-Phase Synthesis of Native Chemical Ligation Precursors” (2) Brooke A. Denslow-Chase, William Smith ’05 (Sep 2004 – May 2005), “Linkers for the Solid-Phase Synthesis of Peptide Thioester Equivalents” (1) Gregory J. Sand, Hobart ’05 (Jul 2004 – May 2005), “Toward the Total Synthesis of Cyclic Peptidic Gene Expression Promoters” PERSONAL INTERESTS Ultimate disc, carpentry, travel/hiking, biking, cooking, arranging and performing vocal music

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